Dimeric procyanidins: screening for B1 to B8 and semisynthetic preparation of B3, B4, B6, And B8 from a polymeric procyanidin fraction of white willow bark (Salix alba)

J Agric Food Chem. 2010 Jul 14;58(13):7820-30. doi: 10.1021/jf101023e.

Abstract

Fifty-seven samples have been analyzed with regard to the occurrence of dimeric procyanidins B1-B8 as well as the composition of polymeric procyanidins. Fifty-two samples were found to contain polymeric procyanidins. In most of the samples, (-)-epicatechin was the predominant unit present. In white willow bark (Salix alba), however, large amounts of (+)-catechin (81.0%) were determined by means of phloroglucinolysis. White willow bark has therefore been used for the semisynthetic formation of dimeric procyanidins B3 [(+)-C-4alpha --> 8-(+)-C)], B4 [(+)-C-4alpha --> 8-(-)-EC)], B6 [(+)-C-4alpha --> 6-(+)-C)], and B8 [(+)-C-4alpha --> 6-(-)-EC)]. The reaction mixtures of the semisynthesis were successfully fractionated with high-speed countercurrent chromatography (HSCCC), and dimeric procyanidins B3, B4, B6, and B8 were obtained on a preparative scale.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Dimerization
  • Plant Bark / chemistry*
  • Plant Extracts / chemical synthesis
  • Plant Extracts / chemistry*
  • Proanthocyanidins / chemical synthesis
  • Proanthocyanidins / chemistry*
  • Salix / chemistry*

Substances

  • Plant Extracts
  • Proanthocyanidins